text: Hydrogen bonding significantly influences the properties of primary and secondary amines. For example, methyl and ethyl amines are gases under standard conditions, whereas the corresponding methyl and ethyl alcohols are liquids. Amines possess a characteristic ammonia smell, liquid amines have a distinctive "fishy" and foul smell.
  The nitrogen atom features a lone electron pair that can bind H to form an ammonium ion RNH. The lone electron pair is represented in this article by two dots above or next to the N. The water solubility of simple amines is enhanced by hydrogen bonding involving these lone electron pairs.  Typically salts of ammonium compounds exhibit the following order of solubility in water: primary ammonium () > secondary ammonium () > tertiary ammonium (RNH). Small aliphatic amines display significant solubility in many solvents, whereas those with large substituents are lipophilic. Aromatic amines, such as aniline, have their lone pair electrons conjugated into the benzene ring, thus their tendency to engage in hydrogen bonding is diminished. Their boiling points are high and their solubility in water is low.